Another great post by Tony Karrer at SoCal CTO -

Are you a non-technical startup founder who’s about to go have a conversation with a Chief Technical Officer (CTO) or Technical advisory type person?   Maybe you are going for a reality check on your current situation – wondering if you have a Weak Development Team or a Startup Founder Developer Gap.  Maybe you are trying to determine what technologies might apply that you should be evaluating.  Maybe you have questions about the types of developers you need and even whether you need a Startup CTO or Developer or both.  Or you want to know about whether you have the right Web Development Company.  Or what else you might need in Document Your MVP for a Developer.

You definitely should be having these conversations in order to find out what things you might not be considering (Questions Developers Should Ask a Startup Founder) that are going to be important to your startup that as a non-technical founder you just don’t know to ask.  And this last one is why I tell every startup founder: Every Web/Mobile Startup Must Have a Technical Advisor.

Of course, when you go to have this conversation be prepared.  I recently had a phone call with an early stage entrepreneur that was incredibly frustrating.  I’d prefer that you don’t make the same mistakes.

Let me lay out at a high level the normal conversation you will have with a strategic technical person:

  • 1 min – small talk
  • 0.25 min (that’s 15 seconds) – why you are meeting
  • 10 minutes – overview of the business and key challenges
  • 30 minutes – questions and thoughts from the technical person

Let me run through these items.

The classic first mistake is to extend the small talk period.  If you’ve not already read How to Hunt Programmers for Your Startup – A Field Guide, go read what motivates and turns off a developer – CTOs and Technical Advisors are quite similar.  Small talk is not a motivator.  It’s not warming us up.  Don’t worry about going straight from “Hi, thanks for meeting with me” to “Well I want to respect your time, so let me dive in.”  Most technical people will appreciate you getting into things quickly.  Small talk is tough work for techies – so much so that people post to help techies with small talk.  Helping you with your challenges is fun.  Oh, and if you read that post, then you know that you will have earned bonus points by buying coffee, beer, whatever for the person as thanks for meeting/helping.  Yes, sadly, that still works on us techies.

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The second item is important to make sure we are on the same page on why we are getting together.  “I have some immediate questions.  I’m hoping to get input on X, Y and Z, but I also want thoughts on what I might not know to ask about.  Depending on where the conversation goes, we may want to talk about how you might be involved in an on-going way.”

The third item is REALLY important.  You need to be prepared to take the technical person through the standard stuff about the business that you would present up to an investor.  Actually, here are two posts with a pretty good list of background items you should plan to cover: Startup Software Development Homework and Free Startup CTO Consulting Sessions.  I personally like when founders have provided me this information prior to meeting for the first time.  It makes sure I know what the business really is, what’s the current state, and gives my analytic brain some time to process things.

A common, but really frustrating, situation is when a startup founder wants to hold back details about the business and product to protect themselves.  As a technical person, I’m sitting there trying to solve a problem.  But the founder is trying to hide the problem.  Argh!  I’m frustrated just thinking about it.  I personally believe the best answer is to provide what you would to an investor.  You don’t ask for an NDA from an investor before presenting.  Don’t ask it from a technical person.  If there’s some really secret sauce, let’s say a special Matching Algorithm, you maybe can hide some of the details of it.

Finally, we get to the fun part.  The technical person will begin to pelt you with questions about the business, product and technical challenges.

We are not trying to be annoying with our questions.  What’s happening is that we’ve translated what you said into initial thoughts around:

  • Business and technical risks  and mitigation strategies
  • Technical challenges and possible solutions
  • Possible third-party technologies that could be used
  • What needs to get researched, architected, built

You know how women complain that men just want to jump right to problem solving.  At the risk of offending lots of people …